Asymmetric cyano-ethoxycarbonylation of aldehydes catalyzed by self-assembled titanium catalyst

Tetrahedron

Volumn 63, Issue 33, 2007, Pages 7935-7941

  Gou, Shaohua ^a   Liu, Xiaohua ^a   Zhou, Xin ^a   Feng, Xiaoming ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Binol; Cyanation; Self assembly; Titanium

Indexed keywords

ACETAMIDE DERIVATIVE; ALDEHYDE; ALDEHYDE DERIVATIVE; CARBONIC ACID; NAPHTHYL GROUP; TITANIUM DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; COMPLEX FORMATION; ENANTIOSELECTIVITY; EXPERIMENTATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 34347240320     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.05.060     Document Type: Article

References (50)

1. For reviews on the syntheses and applications of cyanohydrins, see:
2. North M. In: Murahashi S.-I. (Ed). Science of Synthesis Vol. 19 (2004), Thieme, Stuttgart 235-284
3. Shibasaki M., Kanai M., and Funabashi K. Chem. Commun. (2002) 1989-1999
4. Smith M.B., and March J. March's Advanced Organic Chemistry. 5th ed. (2001), John Wiley & Sons, New York, NY pp 1239-1240
5. Ojima I. Catalytic Asymmetric Synthesis (2000), Wiley, New York, NY pp 235-284
6. Gregory R.J.H. Chem. Rev. 99 (1999) 3649-3682
7. Mori A., and Inoue S. Cyanation of Carbonyl and Amino Groups. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Synthesis (1999), Springer, Heidelberg 983-992
8. Effenberger F. Angew. Chem. 106 (1994) 1609-1619
9. For recent reviews on cyanation reactions, see:
10. Chen F.X., and Feng X.M. Curr. Org. Synth. 3 (2006) 77-97
11. Thierry R.J.A., Lisa A.C., and North M. Synlett (2005) 1828-1847
12. Kanai M., Kato N., Ichikawa E., and Shibasaki M. Synlett (2005) 1491-1508
13. Chen F.X., and Feng X.M. Synlett (2005) 892-899
14. Brunel J.M., and Holmes I.P. Angew. Chem., Int. Ed. 43 (2004) 2752-2778
15. North M. Tetrahedron: Asymmetry 14 (2003) 147-176
16. Gröger H. Chem.-Eur. J. 7 (2001) 5246-5251
17. For selected recent examples, see:
18. Liu X.H., Qin B., Zhou X., He B., and Feng X.M. J. Am. Chem. Soc. 127 (2005) 12224-12225
19. Ryu H.-D., and Corey E.J. J. Am. Chem. Soc. 127 (2005) 5384-5387
20. Fuerst D.E., and Jacobsen E.N. J. Am. Chem. Soc. 127 (2005) 8964-8965
21. Wen Y.H., Huang X., Hang J.L., Xiong Y., Qin B., and Feng X.M. Synlett (2005) 2445-2447
22. Qin Y.C., Liu L., and Pu L. Org. Lett. 7 (2005) 2381-2383
23. Li Y., He B., Qin B., Feng X.M., and Zhang G.L. J. Org. Chem. 69 (2004) 7910-7913
24. Tian S.K., Hong R., and Deng L. J. Am. Chem. Soc. 125 (2003) 9900-9901
25. Casas J., Nájera C., Sansano J.M., and Saá J.M. Org. Lett. 4 (2002) 2589-2592
26. Chen F.X., Zhou H., Liu X.H., Qin B., Feng X.M., Zhang G.L., and Jiang Y.Z. Chem.-Eur. J. 10 (2004) 4790-4797
27. Tian S.K., and Deng L. J. Am. Chem. Soc. 123 (2001) 6195-6196
28. Tian J., Yamagiwa N., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 41 (2002) 3636-3638
29. Yamagiwa N., Tian J., Matsunaga S., and Shibasaki M. J. Am. Chem. Soc. 127 (2005) 3413-3422
30. Baeza A., Nájera C., Sansano J.M., and Saá J.M. Tetrahedron: Asymmetry 16 (2005) 2385-2389
31. Casas J., Baeza A., Sansano J.M., Nájera C., and Saá J.M. Tetrahedron: Asymmetry 14 (2003) 197-200
32. Baeza A., Nájera C., Sansano J.M., and Saá J.M. Angew. Chem., Int. Ed. 42 (2003) 3143-3146
33. Baeza A., Nájera C., Sansano J.M., and Saá J.M. Chem.-Eur. J. 11 (2005) 3849-3862
34. Baeza A., Casas J., Nájera C., Sansano J., and Saá J.M. Eur. J. Org. Chem. (2006) 1949-1958
35. Belokon' Y.N., Blacker A.J., Clutterbuck L.A., and North M. Org. Lett. 5 (2003) 4505-4508
36. Belokon' Y.N., Blacker A.J., Clutterbuck L.A., and North M. Tetrahedron 60 (2004) 10433-10447
37. Lundgren S., Wingstrand E., Penhoat M., and Moberg C. J. Am. Chem. Soc. 127 (2005) 11592-11593
38. Li Q.H., Chang L., Liu X.H., and Feng X.M. Synlett (2006) 1675-1678
39. Gou S.H., Chen X.H., Xiong Y., and Feng X.M. J. Org. Chem. 71 (2006) 5732-5736
40. Chen S.K., Peng D., Zhou H., Wang L.W., Chen F.X., and Feng X.M. Eur. J. Org. Chem. (2006) 639-644
41. Gou S.H., Wang J., Liu X.H., Wang W.T., Chen F.X., and Feng X.M. Adv. Synth. Catal. 349 (2007) 343-349
42. Mikami K., Matasukawa S., Volk T., and Terada M. Angew. Chem. 109 (1997) 2936-2939
43. Mikami K., Terada M., Korenage T., Matsumoto Y., Ueki M., and Angelaud R. Angew. Chem., Int. Ed. 39 (2000) 3532-3556
44. Li X.S., Lu G., Kwok W.H., and Chan A.S.C. J. Am. Chem. Soc. 124 (2002) 12636-12637
45. Hatano M., Miyamoto T., and Ishihara K. Adv. Synth. Catal. 347 (2005) 1561-1568
46. Maruoka K., Itoh T., Araki Y., Shirasaka T., and Yamamoto H. Bull. Chem. Soc. Jpn. 61 (1988) 2975-2976
47. Guo S.Q., Lu N.Y., Liu B., Xiao J., and Li J.S. J. Organomet. Chem. 691 (2006) 1282-1287
48. Lin J., Rajaram A.R., and Pu L. Tetrahedron 60 (2004) 11277-11281
49. Jiang Y.Z., Mi A.Q., Wang Z.Y., and Li S.J. Chin. J. Org. Chem. 14 (1994) 68-73
50. Jiang Y.Z., Qin Y., Mi A.Q., Li Z., Chen X.Z., and Yang D.G. Chin. J. Org. Chem. 16 (1996) 29-33